CN101094902B - Curable silicone compositions incorporating a fluorescent detection system - Google Patents
Curable silicone compositions incorporating a fluorescent detection system Download PDFInfo
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- CN101094902B CN101094902B CN2005800456174A CN200580045617A CN101094902B CN 101094902 B CN101094902 B CN 101094902B CN 2005800456174 A CN2005800456174 A CN 2005800456174A CN 200580045617 A CN200580045617 A CN 200580045617A CN 101094902 B CN101094902 B CN 101094902B
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- 239000000203 mixture Substances 0.000 title claims abstract description 152
- 238000001514 detection method Methods 0.000 title abstract description 4
- 229920001296 polysiloxane Polymers 0.000 title abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 27
- 229910052710 silicon Inorganic materials 0.000 claims description 27
- 239000010703 silicon Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- 239000007850 fluorescent dye Substances 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 16
- 238000013008 moisture curing Methods 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 8
- 229920002050 silicone resin Polymers 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 239000012454 non-polar solvent Substances 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000001723 curing Methods 0.000 description 37
- -1 acrylic ester Chemical class 0.000 description 16
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 10
- 238000000016 photochemical curing Methods 0.000 description 9
- 239000000975 dye Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000004927 fusion Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920001558 organosilicon polymer Polymers 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000004382 potting Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229930006711 bornane-2,3-dione Natural products 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920013730 reactive polymer Polymers 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 125000006227 2-n-butoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- MLOKHANBEXWBKS-UHFFFAOYSA-N 3-triacetyloxysilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](OC(C)=O)(OC(C)=O)OC(C)=O MLOKHANBEXWBKS-UHFFFAOYSA-N 0.000 description 1
- IKVYHNPVKUNCJM-UHFFFAOYSA-N 4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2 IKVYHNPVKUNCJM-UHFFFAOYSA-N 0.000 description 1
- AIXZBGVLNVRQSS-UHFFFAOYSA-N 5-tert-butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical compound CC(C)(C)C1=CC=C2OC(C3=CC=C(S3)C=3OC4=CC=C(C=C4N=3)C(C)(C)C)=NC2=C1 AIXZBGVLNVRQSS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- MFGGXHJEIRBVCP-UHFFFAOYSA-N COC1=C(C(=O)[PH2]=O)C(=CC(=C1)OC)OC Chemical compound COC1=C(C(=O)[PH2]=O)C(=CC(=C1)OC)OC MFGGXHJEIRBVCP-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical class O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QYHJPNQDLVVBDB-UHFFFAOYSA-N ethenyl(trimethoxy)silane;silicon Chemical compound [Si].CO[Si](OC)(OC)C=C QYHJPNQDLVVBDB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- PGXXWBOPUNAGKV-UHFFFAOYSA-N ethylbenzene methane Chemical compound C.C(C)C1=CC=CC=C1 PGXXWBOPUNAGKV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/243—Two or more independent types of crosslinking for one or more polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silicon Polymers (AREA)
Abstract
Description
Claims (13)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US63224704P | 2004-12-01 | 2004-12-01 | |
US60/632,247 | 2004-12-01 | ||
PCT/US2005/041894 WO2006060189A2 (en) | 2004-12-01 | 2005-11-18 | Curable silicone compositions incorporating a fluorescent detection system |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101094902A CN101094902A (en) | 2007-12-26 |
CN101094902B true CN101094902B (en) | 2011-01-19 |
Family
ID=36565528
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2005800456174A Active CN101094902B (en) | 2004-12-01 | 2005-11-18 | Curable silicone compositions incorporating a fluorescent detection system |
Country Status (13)
Country | Link |
---|---|
US (1) | US8013314B2 (en) |
EP (1) | EP1833884B1 (en) |
JP (1) | JP5557983B2 (en) |
KR (1) | KR101201602B1 (en) |
CN (1) | CN101094902B (en) |
CA (1) | CA2588842C (en) |
DK (1) | DK1833884T3 (en) |
ES (1) | ES2546107T3 (en) |
HU (1) | HUE05848930T2 (en) |
MX (1) | MX2007006609A (en) |
PL (1) | PL1833884T3 (en) |
PT (1) | PT1833884E (en) |
WO (1) | WO2006060189A2 (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100224305A1 (en) * | 2009-03-04 | 2010-09-09 | Stephen Paul Zadesky | Adhesive Having UV-Reactive Colorization |
US8871317B2 (en) | 2010-09-09 | 2014-10-28 | Teknor Apex Company | Curable adhesive system, method of assembly of distinct components therewith |
CN102532434B (en) * | 2011-12-13 | 2014-09-17 | 北京海斯迪克新材料有限公司 | UV (Ultraviolet)/moisture double cured silicon rubber and preparation method thereof |
DE102012220574A1 (en) | 2012-11-12 | 2014-05-15 | Tesa Se | Composition useful for release coating, detecting defects during application of release coating on substrate, and producing release layer of release liner, comprises release agent, and at least one optical brightener or at least one pigment |
JP2014203806A (en) * | 2013-04-10 | 2014-10-27 | 矢崎総業株式会社 | Water stop structure for electric wire and production method thereof |
KR20140129934A (en) * | 2013-04-30 | 2014-11-07 | 제일모직주식회사 | Photocurable composition and encapsulated apparatus comprising the same |
CN103965821B (en) * | 2014-04-30 | 2016-03-16 | 京东方科技集团股份有限公司 | A kind of sealant composition and display unit |
CN108699388B (en) * | 2016-03-07 | 2020-09-25 | 美国陶氏有机硅公司 | Photocurable silicone composition and cured product thereof |
KR102468361B1 (en) | 2016-03-22 | 2022-11-18 | 삼성디스플레이 주식회사 | Display device and method of manufacturing the same |
US10035911B2 (en) * | 2016-05-19 | 2018-07-31 | Momentive Performance Materials Inc. | Curable, dual cure, one part silicone composition |
AU2017370407B2 (en) * | 2016-12-09 | 2020-07-23 | Momentive Performance Materials Korea Co., Ltd | Composition for organic electronic element encapsulant and encapsulant formed using same |
TWI782066B (en) | 2017-08-03 | 2022-11-01 | 德商漢高股份有限及兩合公司 | Curable silicone optically clear adhesives and uses thereof |
WO2019133580A1 (en) | 2017-12-27 | 2019-07-04 | Henkel IP & Holding GmbH | Optically clear pressure sensitive adhesives and uses thereof |
US20210070945A1 (en) | 2019-09-06 | 2021-03-11 | Elkem Silicones USA Corp. | Process and premix for incorporating optical brighteners into a polymeric composition |
KR102271413B1 (en) * | 2020-10-20 | 2021-06-30 | 김효남 | Photoluminescent silicone composition and method and silicone container |
WO2023078980A1 (en) * | 2021-11-04 | 2023-05-11 | Loparex Germany Gmbh & Co. Kg | Identification of silicone defects during running coating operation |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5240971A (en) * | 1991-12-05 | 1993-08-31 | General Electric Company | UV-curable epoxysilicone-polyether block copolymers |
US5792589A (en) * | 1996-02-06 | 1998-08-11 | Japan Synthetic Rubber Co., Ltd. | Radiation sensitive composition containing a fluorescent substance dispersed therein |
US6103453A (en) * | 1998-03-24 | 2000-08-15 | Basf Aktiengesellschaft | Photoinitiator blends |
US6251962B1 (en) * | 1997-02-19 | 2001-06-26 | Ciba Specialty Chemicals Corporation | (Co)polymers by photopolymerization |
US6627672B1 (en) * | 2001-05-16 | 2003-09-30 | Henkel Loctite Corporation | UV/moisture dual cure silicone potting compound with improved depth of cure |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4111890A (en) | 1977-12-19 | 1978-09-05 | Sws Silicones Corporation | Curable organopolysiloxane compositions containing titanium esters |
DE2909994A1 (en) * | 1979-03-14 | 1980-10-02 | Basf Ag | ACYLPHOSPHINOXIDE COMPOUNDS, THEIR PRODUCTION AND USE |
US4528081A (en) | 1983-10-03 | 1985-07-09 | Loctite Corporation | Dual curing silicone, method of preparing same and dielectric soft-gel compositions thereof |
US4699802A (en) | 1983-10-03 | 1987-10-13 | Loctite Corporation | Dual curing coating method for substrates with shadow areas |
CA1337224C (en) * | 1987-11-06 | 1995-10-03 | Beth I. Gutek | Compositions having uv cure with moisture shadow cure |
US4966922A (en) * | 1988-06-09 | 1990-10-30 | General Electric Company | Dual curable silicone compositions |
US5227410A (en) * | 1991-12-05 | 1993-07-13 | General Electric Company | Uv-curable epoxysilicone-polyether block copolymers |
US5162390A (en) * | 1990-03-05 | 1992-11-10 | General Electric Company | UV curable coating compositions, abrasion resistant UV stabilized thermoplastic composites and method |
US5348986A (en) | 1990-11-19 | 1994-09-20 | Loctite Corporation | Photocurable silicone composition, and method of making same |
EP0711801B1 (en) * | 1990-12-28 | 1999-10-06 | Dow Corning Corporation | Method of indicating a cure point for ultraviolet radiation curing compositions by color change |
EP0505737A1 (en) * | 1991-03-27 | 1992-09-30 | General Electric Company | UV curable abrasion resistant coating compositions and method |
US5300608A (en) * | 1992-03-31 | 1994-04-05 | Loctite Corporation | Process for preparing alkoxy-terminated organosiloxane fluids using organo-lithium reagents |
US5516812A (en) | 1992-03-31 | 1996-05-14 | Loctite Corporation | UV-moisture dual cure silicone conformal coating compositions with improved surface tack |
US5498642A (en) | 1992-03-31 | 1996-03-12 | Loctite Corporation | Radiation surface-curable, room temperature vulcanizing silicone compositions |
US5663269A (en) | 1992-03-31 | 1997-09-02 | Loctite Corporation | Organosiloxane fluids prepared using organo-lithium reagents |
US5707781A (en) * | 1995-05-05 | 1998-01-13 | Bayer Corporation | Photopolymerizable compositions having acyl or diacyl phosphine oxide and a fluorescent optical brightner |
US5801884A (en) * | 1995-10-09 | 1998-09-01 | Mitsubishi Chemical Corporation | Optical device and process for producing the same |
US6080450A (en) | 1996-02-23 | 2000-06-27 | Dymax Corporation | Composition exhibiting improved fluorescent response |
DE19650562A1 (en) * | 1996-12-05 | 1998-06-10 | Basf Ag | Mixtures of photoinitiators containing acylphosphine oxides and benzophenone derivatives |
US6323253B1 (en) * | 1998-06-01 | 2001-11-27 | Loctite Corporation | Flame-retardant UV and UV/moisture curable silicone compositions |
BR9911490A (en) | 1998-06-24 | 2001-03-20 | Loctite Corp | Silicone composition cured by radiation and moisture, and, process for preparing the composition |
US6140444A (en) | 1999-01-19 | 2000-10-31 | Loctite Corporation | Catalyst system, process, and silicone compositions |
CA2324794A1 (en) * | 2000-10-25 | 2002-04-25 | American Dye Source, Inc. | Organic-inorganic hybrid photocurable compositions |
JP3786408B2 (en) * | 2001-11-15 | 2006-06-14 | 日本化薬株式会社 | Energy ray curable resin composition |
AU2002357674A1 (en) * | 2002-02-05 | 2003-09-02 | Henkel Corporation | Luminescing and/or fluorescing radiation-curable, cyanoacrylate-containing compositions |
TW200613391A (en) * | 2004-09-01 | 2006-05-01 | Novartis Ag | Method for making colored silicone hydrogel contact lenses |
-
2005
- 2005-11-18 US US11/720,611 patent/US8013314B2/en active Active
- 2005-11-18 ES ES05848930.3T patent/ES2546107T3/en active Active
- 2005-11-18 KR KR1020077014929A patent/KR101201602B1/en active IP Right Grant
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- 2005-11-18 MX MX2007006609A patent/MX2007006609A/en active IP Right Grant
- 2005-11-18 EP EP05848930.3A patent/EP1833884B1/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5240971A (en) * | 1991-12-05 | 1993-08-31 | General Electric Company | UV-curable epoxysilicone-polyether block copolymers |
US5792589A (en) * | 1996-02-06 | 1998-08-11 | Japan Synthetic Rubber Co., Ltd. | Radiation sensitive composition containing a fluorescent substance dispersed therein |
US6251962B1 (en) * | 1997-02-19 | 2001-06-26 | Ciba Specialty Chemicals Corporation | (Co)polymers by photopolymerization |
US6103453A (en) * | 1998-03-24 | 2000-08-15 | Basf Aktiengesellschaft | Photoinitiator blends |
US6627672B1 (en) * | 2001-05-16 | 2003-09-30 | Henkel Loctite Corporation | UV/moisture dual cure silicone potting compound with improved depth of cure |
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WO2006060189A2 (en) | 2006-06-08 |
US20090166559A1 (en) | 2009-07-02 |
EP1833884A2 (en) | 2007-09-19 |
CA2588842A1 (en) | 2006-06-08 |
MX2007006609A (en) | 2007-08-14 |
PL1833884T3 (en) | 2015-12-31 |
EP1833884A4 (en) | 2009-05-27 |
EP1833884B1 (en) | 2015-06-24 |
US8013314B2 (en) | 2011-09-06 |
KR101201602B1 (en) | 2012-11-14 |
ES2546107T3 (en) | 2015-09-18 |
KR20070089834A (en) | 2007-09-03 |
CN101094902A (en) | 2007-12-26 |
JP2008522006A (en) | 2008-06-26 |
JP5557983B2 (en) | 2014-07-23 |
HUE05848930T2 (en) | 2016-05-30 |
DK1833884T3 (en) | 2015-09-28 |
CA2588842C (en) | 2012-09-11 |
PT1833884E (en) | 2015-10-05 |
WO2006060189A3 (en) | 2006-09-14 |
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